Tracking down Fred Eychaner, one of the most reclusive—and powerful—donors in Democratic politics, was no easy task.

Increasingly, political journalists are treating super PAC mega-donors as major public figures—and many of these extremely rich individuals have embraced or at least accepted the resulting spotlight. Tom Steyer, the liberal hedge-fund billionaire crusading for environmental protection, has been making the press rounds of late like a Hollywood actor promoting a movie. Even the media-averse Koch brothers are publicly explaining themselves more and more these days—most recently with Charles Koch penning an op-ed in The Wall Street Journal.

Yet one mega-donor has managed to stay almost completely out of the public eye: Fred Eychaner. The Chicago businessman gave an astounding $14.1 million to liberal super PACs in 2012, making him the largest Democratic donor to outside spending groups during that election cycle. The following year, Eychaner, who is gay, also helped to organize and fund a successful effort to pass same-sex-marriage legislation in Illinois. But Eychaner has an extreme allergy to publicity, and thus is rarely written about in much detail. Only a handful of public photos of him exist. And although he will very infrequently indulge questions about his art-related philanthropy, he had—as of earlier this year—not discussed his political efforts with a reporter since 2005.

This past December, I began asking around about Eychaner. Not surprisingly, over the following months I had a hard time getting many details. "He is a very, very smart, discerning guy," David Axelrod, President Obama's former senior adviser, told me. "He doesn't travel in a pack," offered Chicago Mayor Rahm Emanuel, a longtime recipient of Eychaner's money. "He is probably the biggest donor who is not an ambassador or wanted to be an ambassador," said Lynn Cutler, a former vice chairwoman of the Democratic National Committee.

"He has such a low public profile," said Robert Feder, a Chicago reporter who has covered Eychaner's media holdings over the years. "One-on-one, he is modest and humble and unassuming. Everything is very closely guarded. We can only surmise things based on what he has done and deals he has made and gifts he has given."

It's not just journalists who are kept at bay. Even some political friends who once had a direct line of access to Eychaner told me he has become less and less accessible in recent years. Almost everyone now gets routed through Dave Horwich, a former advance staffer for Bill Clinton and the Clinton Foundation who is currently vice president of Eychaner's printing and media company, Newsweb.

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At the outset of my reporting, I left both Horwich and Eychaner's secretary messages about my interest in profiling their boss. In early January, Horwich called me somewhat out of the blue. "Why are you doing this?" he said in a tone that sounded half-exasperated, half-lighthearted. He had been getting calls—from sources I was contacting to ask about Eychaner—alerting him to my doings.

What followed was a months-long vetting process, much of it conducted through off-the-record conversations over the phone and in person. But eventually, Fred Eychaner—perhaps the most mysterious figure in Democratic Party politics—agreed to be interviewed.

"I DON'T WANT TO BE A PLAYER"

Eychaner and I met twice over the course of several days—first at a diner on Chicago's North Side (he ordered "just plain turkey"), next at a breakfast place in Lincoln Park (separated egg whites and raisin toast). At 69, he is slender and bald, with some cropped grizzle around his temples, thin glasses, and two hearing aids.

More than wanting to tell me who he is, Eychaner seemed intent on telling me who he is not.

To our first interview, he wore a white button-down shirt from the Gap and black pants, and carried with him a worn leather binder containing a notepad and news clippings. Over the next hour, he rendered himself largely unquotable by frequently interrupting his own thoughts, mid-sentence, to apologize or insist we go off the record whenever he sensed his words were censorious or self-aggrandizing (which they weren't). He was adamant about not wanting to offend others or "toot my own horn."

More than wanting to tell me who he is, Eychaner seemed intent on telling me who he is not. In various accounts, he has been referred to as a "broadcasting tycoon," a "media mogul," a "reclusive and ascetic media millionaire," and so on. He chafes at these labels. He is not a tycoon, he said, because a tycoon possesses a certain commanding disposition toward life and his station in it. "I am not Richard Branson," he said—then made clear he meant no offense to Branson.

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Eychaner took particular umbrage at the term "player," as it is used to describe those unelected types in politics who matter. "It is not a scorecard, but that's what the media has turned politics into," he said. "I hate that. I don't want to be a player." So how would he define himself then? He blandly demurred: "I am a basic social activist with small-business experience, and you go where you need to go."

Eychaner grew up in suburban Chicago, the son of middle-class parents. When he sat down for our second breakfast, he handed me a piece of yellow notebook paper, on which he had typed seven short paragraphs of notes relating to our first conversation. It began: "Growing up—mother only one in their generation [on] either side who went to college. Elementary school teacher, married my father and was fired because female school teachers were supposed to be single." Working off his note sheet, I asked Eychaner about his father, who operated a moving-and-storage business in their hometown of DeKalb, Ill. Eychaner started telling me about how his dad built up the company. But then he abruptly stopped the story. "I don't want to be a bleeding heart over this," he said.

One of the strangest things about Eychaner, given his aversion to publicity, is that he gravitated toward journalism as a young man. In high school, he worked at the local newspaper, The Daily Chronicle, "but I wasn't a great employee," he said. Still, after graduating from Northwestern and hitchhiking around Latin America, Eychaner decided to pursue a master's degree in journalism, also at Northwestern. "I know you in your generation are all about storytelling," he told me. "We were about truth-seeking." While in grad school, he started a printing business that served alternative weekly and community newspapers. Eventually, he told me, he was kicked out of the program because he repeatedly missed a morning reporting class so he could tend to his fledgling company.

Eychaner's initial spoils in the business world came from some smart investments in closely held private media corporations, including the parent company of The Des Moines Register. But it was his foray into television that turned him into a very wealthy man. It began in the early 1980s, when he spent $1.5 million for a dormant permit to build TV antennas in northwest Indiana. Through a series of negotiations, he traded up to take control of Channel 50 in Chicago, then spent the next several years building the station's audience through a number of well-considered programming acquisitions (Roseanne; Star Trek: The Next Generation).

In 2002, he sold the station to Rupert Murdoch for $425 million. "This was the most astonishing deal I have witnessed in covering media in Chicago," says Feder. "It takes my breath away when I think of it now.... He outfoxed Murdoch, which rarely happens for anyone." (A spokesman for Murdoch did not respond to a request for comment.) For his part, Eychaner laughed off the notion that he got the better of anybody. "Objectively, the industry was consolidating rapidly, and they executed their strategy," he said. "It wasn't an individual outfoxing as much as it was a global change." He then promptly changed the subject to the first and only time he met Murdoch, years before the sale—when Eychaner arrived at a meeting of television executives with a giant hole in his pants. (He had ripped them on a food-service cart on the flight over.)

A large chunk of the Channel 50 sale's proceeds went to the Alphawood Foundation, Eychaner's $100 million philanthropic organization, which has sponsored everything from HIV awareness to dance troupes. Last year, the foundation gave a $32 million gift to a British university to help fund an Asian arts program.

But Eychaner's interests were not solely in apolitical charity. Since the 1980s, he has donated to progressive local candidates in Chicago. In 1992, he started to play on the national stage, supporting Bill Clinton's presidential campaign, even though Jimmy Carter's reelection flop had left him "disenchanted by Southern governors."

When it comes to his political donations, Eychaner has consistently used a very simple, partisan formula. "At the end of the day, are we better off with Republicans or Democrats?" he said. In his mind, it's the latter, so he refrains from donating to Republicans, no matter how moderate, and he tries to avoid spending any money in contested federal primaries. (That said, he did support Hillary Clinton's 2008 presidential primary bid against Barack Obama—a break from the Chicago Democratic establishment. He noted that this decision was partly a function of loyalty, and partly because he thought Clinton would be stronger on LGBT issues.)

When I asked Eychaner why he supported super PACs when so many other Democrats didn't—Obama's stated opposition to Citizens United put a damper on progressive fundraising in 2012—he explained that he never bought into Nate Silver's projections or the confidence expressed by some in the Obama campaign. He said he was surprised at the end of the cycle that he wound up as the largest Democratic super PAC donor. He also said that while he was happy with the money he spent, he remains "totally opposed to Citizens United."

"I AM NOT THE PROGRESSIVE KOCH BROTHER"

Eychaner came out to his parents by the late 1980s—"I had been dropping clues along the way," he said—but he decided to make a more public acknowledgment of his sexual orientation in the April 1993 issue of Broadcasting & Cable magazine. Al DeVaney, Eychaner's then-station manager, told me he was shocked when his boss came to him stating his intentions—it seemed distinctly unlike Eychaner. In the end, the only reference to Eychaner's sexuality was in an info box that accompanied the magazine's profile, which listed Eychaner's then-boyfriend as his partner. (When I asked Eychaner if he was in a relationship now, he declined to say.)

Much of the LGBT infrastructure in Chicago bears Eychaner's stamp. He is the largest donor to the AIDS Foundation of Chicago, and he was instrumental in the formation of Equality Illinois—the state's most influential gay-rights advocacy group—as well as the Midwest chapter of the Lambda Legal Defense and Education Fund. (To our second lunch, he brought me a copy of And The Band Played On, the 1987 best seller about the AIDS epidemic, which he had alluded to a few days before when discussing Bill Clinton's pragmatic approach to gay rights.)

Same-sex-marriage legislation was first introduced in the Illinois Legislature in 2007, but it failed to get out of committee. It wasn't until the bill was reintroduced last year that it seemed ready to make it to the floor. Eychaner decided to construct his own heavily funded lobbying and public-relations vehicle instead of donating funds to existing gay-rights groups. To do his media, he hired ASGK Public Strategies, a Chicago-based PR firm with ties to Obama, and he enlisted several of the state's top lobbyists.

Eychaner entrusted Mike Madigan—the powerful Democratic speaker of the Illinois House of Representatives and someone to whom he had been a generous donor over the years—to deliver the votes. This did not sit well with other advocates, who wanted to cast a wider lobbying net, as opposed to leaning so heavily on Madigan to round up support.

"I would go on the record with my respect for Mike Madigan, which will probably upset a lot of friends," Eychaner says now. "He's enormously skillful at what he does. The only speakers of any House who survive are the ones who can keep their majority and keep everyone going largely in the same direction. Mike Madigan is superb at that."

When it appeared last summer that they didn't have the votes, the Legislature's gay-marriage supporters delayed calling the bill to the floor. The grassroots wing of the LGBT movement was upset, and some began blaming Eychaner. The most obstreperous of these critics, a longtime gay-rights activist named Rick Garcia, publicly chastised Eychaner for being in Madigan's pocket.

But after a five-month delay, the bill was voted on and passed, marking a historic occasion as well as vindicating Eychaner's strategy. Eychaner compared the process to 20 mad chefs cooking on 20 different burners. "The person to the left of you by one degree thinks you're selling out," he said. "You've got to do what you've got to do. I don't think I'll be in that position again."

When I asked about his near-term plans, he indicated only his interest in putting money behind the reelection campaign of Illinois Gov. Pat Quinn whose self-funding Republican opponent, Bruce Rauner, busted the individual spending-limits cap in the primary. "I don't expect to be among the top donors this year, but I will do my share," he said. "I am not the progressive Koch brother." David and Charles Koch (Marc Stamas/Getty Images, left, and Jamie Kripke/Forbes Collection/Corbis Outline)

Even after two lunches with Eychaner, this was about as good an answer as I could get. I had expected to find a man who, although reserved, would project a sense of confidence and purpose about how he was going to follow up his 2012 and 2013 political triumphs. Instead, I found someone who seemed nervous, shy, and self-effacing. Someone who hemmed and hawed and blushed and buried his hands in his face and rubbed his temples and tried repeatedly to change the subject back to me. Someone who projected genuine irresolution about how he planned to carry forth politically.

Or maybe he knew better than he was letting on. In mid-April, campaign finance filings showed that Eychaner had donated $4 million to Senate Majority PAC, which once again thrusts him into the upper echelon of super PAC mega-donors. Then, later that month, on April 23, Eychaner gave a rare public speech while accepting a lifetime achievement award from Lambda Legal. He stood at a lectern at the Art Institute of Chicago, smiling and at ease, as he recalled the decades-long fight for LGBT equality. He spoke of his parents as "teetotaling Methodists" who became actively involved in the gay-rights movement. He condemned Reagan-era conservatives for "demonizing" the movement, adding: "The hatred they sowed during those years continues to ricochet today."

"They have done the same dehumanization of progressives of all kinds," he said, as a photographer snapped pictures of him from the front row. "They race-bait people of color as they try to obstruct their voting rights. They are trying to again interfere with a woman's right to free choice."

It was, by any account, his most demonstrative and revealing public display yet. And it was a sign, I think, of a new reality, not just for Eychaner but for political mega-donors of all kinds: If you give enough money, you will at some point face enormous pressure to step in front of the cameras and define yourself—lest your opponents do it for you. There's simply too much media interest and scrutiny these days for it to be any other way.

As I watched Eychaner's speech on YouTube, I saw a man who seemed to have accepted this reality. For three months, I'd been thinking of myself as Fred Eychaner's meddling beseecher. Maybe, instead, I was his warm-up act.

The author is a Chicago-based writer who has previously worked for Politico and The Daily.